Trifluoroacetic acid → 2-(4-Nitrophenyl)ethyl pyrrolo[4,5-e]indoline-7-carboxylate

HRID 599376Notes

Reaction equation

HRID 599376 reaction equation
C(OC([N:8]1[C:19]2[C:11](=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]([C:20]([O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=2)=[O:21])[CH2:13]3)[CH:10]=[CH:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>>[CH:10]1[C:11]2=[C:12]3[C:16](=[CH:17][CH:18]=[C:19]2[NH:8][CH:9]=1)[NH:15][CH:14]([C:20]([O:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:21])[CH2:13]3

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 667170292-(4-Nitrophenyl)ethyl3-[(tert-butyl)oxycarbonyl]pyrrolo[4,5-e]indoline-7-carboxylate

Product 1

HCID 667170282-(4-Nitrophenyl)ethyl pyrrolo[4,5-e]indoline-7-carboxylate

Procedure

Two grams (4.43 mmol) of 14 are weighed into a round bottomed flask. Then, in a fume hood, 25 mL (325 mmol) of trifluroacetic acid is added, and the flask is capped and stirred. The solid dissolves in about a minute. The mixture is stirred for 1 hour, at which time deprotection will be done (HPLC can be used as a check). The acid is evaporated on a rotary evaporator (use a trap) and the product is dissolved in 100 mL of methylene chloride. This is extracted twice with 100 mL of half to ⅔ saturated sodium bicarbonate solution. The aqueous layers are back-extracted once with ˜50 mL of methylene chloride and this is combined with the rest. The organic layer is dried over sodium sulfate twice and evaporated to give a brown solid. If desired, this material can be recrystallized by diluting a very concentrated solution in methylene chloride with methanol and cooling.

Workup

  1. customthe flask is capped
  2. dissolutionThe solid dissolves in about a minute
  3. stirringThe mixture is stirred for 1 hour, at which time deprotection
  4. customThe acid is evaporated on a rotary evaporator (use a trap)
  5. dissolutionthe product is dissolved in 100 mL of methylene chloride
  6. extractionThis is extracted twice with 100 mL of half
  7. extractionThe aqueous layers are back-extracted once with ˜50 mL of methylene chloride
  8. dry with materialThe organic layer is dried over sodium sulfate twice
  9. customevaporated
  10. customto give a brown solid
  11. customthis material can be recrystallized
  12. additionby diluting a very concentrated solution in methylene chloride with methanol
  13. temperaturecooling

Sources & evidence

ORD record
ord-8b651f164a374d47a90f70e6a1bb924c
Source dataset
uspto-grants-2011_03
Patent number
US07897736B2

Reaction notes

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